WO2008025589A1 - Agent de dégivrage et/ou antigivre - Google Patents

Agent de dégivrage et/ou antigivre Download PDF

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Publication number
WO2008025589A1
WO2008025589A1 PCT/EP2007/056895 EP2007056895W WO2008025589A1 WO 2008025589 A1 WO2008025589 A1 WO 2008025589A1 EP 2007056895 W EP2007056895 W EP 2007056895W WO 2008025589 A1 WO2008025589 A1 WO 2008025589A1
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WO
WIPO (PCT)
Prior art keywords
deicing
icing
agent according
icing agent
weight
Prior art date
Application number
PCT/EP2007/056895
Other languages
German (de)
English (en)
Inventor
Matthias Seiler
Stefan Bernhardt
Original Assignee
Evonik Degussa Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Evonik Degussa Gmbh filed Critical Evonik Degussa Gmbh
Priority to JP2009526000A priority Critical patent/JP2010501692A/ja
Priority to AT07787177T priority patent/ATE466062T1/de
Priority to EP07787177A priority patent/EP2054483B1/fr
Priority to CA002661262A priority patent/CA2661262A1/fr
Priority to DE502007003618T priority patent/DE502007003618D1/de
Priority to US12/310,318 priority patent/US7875203B2/en
Publication of WO2008025589A1 publication Critical patent/WO2008025589A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces

Definitions

  • the present invention relates to dendritic polymers thickened water / glycol mixtures which can be used as deicing and / or anti-icing agents, in particular as anti-icing agents. These mixtures are used to remove frozen precipitates, such as ice and snow, from surfaces and to prevent re-icing of these surfaces.
  • deicers which are used primarily for the removal of frozen precipitation
  • anti-icing agents which are to counteract already de-iced and thus cleaned aircraft surfaces re-icing.
  • Aircraft deicing must meet a large number of requirements. According to the SAE specifications AMS (Aerospace Material Standards) 1424 and AMS 1428 not only the discharge behavior and the anti-icing time are investigated, but also many other physical properties. This includes, for example, the storage stability of the aircraft deicing agents. The viscosity of the aircraft deicing composition should as far as possible not change during storage over a longer period of time. A good aircraft deicing should not be corrosive, especially not against aluminum, magnesium, steel and acrylic glass. It should be as environmentally friendly as possible and should not support fires if possible.
  • thickened aircraft deicing agents should be as shear stable as possible.
  • the fluids are applied by spraying vehicles, which cause a high mechanical load of the fluid.
  • the deicers should lose as little as possible of their original viscosity.
  • Precipitation water / glycol based deicers used.
  • the glycol serves as a freezing point depressing medium.
  • surfactants are included which reduce the surface tension of the deicing composition and thus improve the wetting of the aircraft surfaces.
  • deicing agents may contain corrosion inhibitors, defoamers, dyes and flame retardants. Such non-thickened deicers are characterized by Newtonian flow behavior. This means that their viscosity is shear-independent.
  • Type I fluids According to the SAE (Society of Automotive Engineering) convention, non-thickened de-icers with Newtonian flow behavior are referred to as Type I fluids.
  • Type I fluids are diluted depending on the outside temperature with a different amount of water and with Sprayers hot applied to the aircraft surfaces. With their help, frozen deposits can be effectively removed.
  • Type I fluids have very limited protection against re-icing.
  • Such a deicing agent is z. As described in WO 94/05741. It relates to a deicing composition containing 25% to 95% glycol, a pH regulator which adjusts the pH of the agent to 7 to 10, and at least one nonionic or anionic surfactant.
  • anti-icing agents In contrast to pure deicing agents, anti-icing agents additionally contain thickeners. The resulting viscosity of these fluids improves the protection against re-icing, because the fluid flows at rest only very slowly from the aircraft surfaces and can thus absorb over a longer period of freezing precipitation.
  • Anti-icing agents obtained by the thickening agent used here a non-Newtonian, pseudoplastic flow behavior. The viscosity of these fluids is shear dependent. At the moment of the aircraft take-off, the viscosity of the fluid drops very sharply due to the increasing air resistance, and thus it can quickly flow away from the aircraft surfaces.
  • Type II and Type IV fluids a distinction is made between Type II and Type IV fluids. Type III fluids are characterized by a particularly pseudo-plastic flow behavior, so that they serve for deicing of low-speed aircraft.
  • thickeners are usually organic polymers, such as. B. crosslinked homopolymers or copolymers of unsaturated carboxylic acids such as acrylic acid, methacrylic acid and their derivatives, such as esters and amides, also cellulose ethers (alkyl, hydroxyalkyl and carboxyalkylcellulose ethers), polyethylene glycols, polyvinylpyrrolidones, polyvinyl alcohols, polyethylene oxides, xanthan gum and the like, or mixtures of such water-soluble polymers used.
  • the thickening mechanism of all these organic polymers is based on the formation of a polymer network in the glycol solution.
  • WO 93/24543 describes anti-icing agents based on an aqueous glycol solution comprising a comb polymer with hydrophilic polymer backbone and hydrophobic side chains as thickening agent.
  • EP 0 769 541 A1 discloses a deicing and anti-icing agent for aircraft comprising as thickener water-soluble crosslinked acrylic homopolymers, from 0.02% to 1.5% by weight of at least one nonionic surfactant and
  • the acrylic polymer has an average molecular weight of 750,000 g / mol to 1,250,000 g / mol and has in the form of a 0.5 wt .-% aqueous solution having a pH of 7.0 and a temperature of 20 0 C. a viscosity of 1000 mPa.s to 13,000 mPa.s, measured as Brookfield viscosity at 20 rpm.
  • WO 98/46695 relates to a deicing or anti-icing agent comprising 35.0% to 80.0% by weight of glycol, water, a first nonionic surfactant having an HLB in the range of 4 to 17, a second nonionic surfactant having an HLB in the range of 5 to 18, a
  • Polycarboxylate as emulsifier and a pH regulator contains.
  • thickeners mentioned are damaged more or less irreversibly under mechanical stress. This is evidenced by an irreversible loss of viscosity due to high shear stress caused by high-speed stirrers, pumps or when flowing through small pipe cross-sections.
  • the mechanical stress causes a fracture of the polymer chains and associated irreversible damage to the polymer network.
  • Aircraft anti-icing agents which lose as little viscosity as possible under mechanical stress, such as pumping or spraying with sprayers.
  • the thickeners mentioned tend to gel under certain external conditions. If aviation anti-icing agents accumulate in aerodynamically quiet areas of the aircraft after take-off, these residues completely dry up due to the low air pressure at flight heights of 5,000 m or more. These residues can swell greatly if they come in contact with moisture such as rainwater. The resulting gels can freeze at low temperatures, such as those encountered at high altitudes, thereby blocking the elevator, rendering the aircraft incapable of complete maneuverability.
  • the aircraft anti-icing agents based on conventional thickening agents form clearly visible amounts of gel residue.
  • these gels can be mixed with the water during rehydration replace more or less well.
  • European patent application EP 1 553 152 A2 proposes a deicing or anti-icing agent which comprises at least 35% to 93% by weight of at least one glycol and from 0.01% to 15% by weight a water-soluble phyllosilicate and water.
  • Disadvantage is that sometimes high concentrations of water-soluble phyllosilicates are necessary to achieve a thickening effect.
  • agglomeration of the phyllosilicates may occur, especially after prolonged storage of the anti-icing agent, which necessitates re-dispersion or the use of dispersing additives.
  • the property profile of the deicing and anti-icing agents should be improved in at least one, preferably as many as possible, of the following:
  • Anti-icing agents in the simplest possible way, be available on an industrial scale and inexpensively.
  • a deicing or anti-icing agent which, based on its weight, comprises 35.0% by weight to 95.0% by weight of at least one glycol, 0.001% by weight to 5.0% by weight. % of at least one dendritic polymer and 0.01 wt .-% to 5.0 wt .-% of at least one other thickener and optionally water, succeeds in not easily foreseeable manner, a deicing or anti-icing agent with significantly improved property profile accessible to do, which is characterized in particular by the following features:
  • the agent has a comparatively high storage stability
  • the agent is not corrosive, especially not aluminum, magnesium, steel and acrylic glass,
  • the agent has a comparatively low toxicity
  • the remedy is not fire-promoting
  • Shear stability and usually does not lose more than 30%, preferably not more than 25% and most preferably not more than 20%, of its original viscosity
  • dendritic polymers employed generally are not prone to gelation with water and are further characterized by generally excellent solubility in aqueous (polar) systems; nevertheless small amounts of gel formed can therefore easily be rinsed off by water,
  • the dendritic polymers used adsorb on any forming crystal growth surfaces and thus slow or prevent the crystallization of components of the agent, such as. B. corrosion inhibitors, flame retardants, the agent shows a comparatively high shear thinning, ie it has a comparatively high viscosity at low shear forces and a comparatively low viscosity at high shear forces,
  • the dendritic polymers used can, due to the large number of functional groups, be mixed with the thickener, eg. Through hydrogen bonds or other polar interactions, form a physical network that dissolves upon shear stress (eg, when an aircraft is launched) and allows the agent to drain.
  • the present invention thus provides a de-icing or anti-icing agent which, based in each case on its total weight, 35.0 wt .-% to 95.0 wt .-% of at least one glycol, 0.001 wt .-% to 5.0 wt. -% of at least one dendritic polymer and 0.01 wt .-% to 5.0 wt .-% of at least one further thickening agent and preferably water.
  • Another object of the invention is the use of 0.001 wt .-% to 5.0 wt .-% of at least one dendritic polymer and 0.01 wt .-% to 5.0 wt .-% of at least one other thickening agent for thickening a composition containing 35.0 wt .-% to 95.0 wt .-% of at least one glycol and preferably water.
  • a deicing composition and / or anti-icing agent according to the invention may, in a preferred embodiment, comprise the following constituents:
  • Carboxylic acids such as acrylic acid, methacrylic acid and their derivatives, such as esters and amides, furthermore cellulose ethers (alkyl, hydroxyalkyl and carboxyalkylcellulose ethers), polyethylene glycols, polyvinylpyrrolidones, polyvinyl alcohols, polyethylene oxides, xanthan gum,
  • the percentages by weight always refer to the weight of the deicing or anti-icing agent.
  • the constituents b, c, f, g and h are not necessarily contained in the deicing composition or anti-icing agent according to the invention.
  • preferred deicing or anti-icing agents contain, in addition to components a, d and e, one or more further constituents b, c, f, g and h.
  • the component a) of the deicing composition or the anti-icing agent according to the invention is preferably ethylene glycol, propylene glycol (1, 2-propylene glycol or 1, 3-propylene glycol), diethylene glycol, dipropylene glycol or a mixture of two or more of these glycols, with propylene glycols being particularly preferred.
  • the glycols are mainly used to lower the freezing point and represent water in addition to the main component of the deicing agent.
  • Component b) may preferably be a fatty alcohol having 6 to 24 C atoms, preferably 8 to 18 C atoms in the alkyl radical or an alkoxylate thereof having 1 to 10, preferably 1 to 8 alkoxy groups, in particular of ethylene oxide, propylene oxide or a mixture thereof with ethylene oxide being preferred.
  • the abovementioned alkyl radical in the fatty alcohol can be straight or branched, aliphatic or aromatic, saturated or unsaturated, with preferably 1 to 3 double bonds. Examples include: octyl, decyl, dodecyl, isotridecy, para-iso
  • the component b) may also be a mixture of said fatty alcohols and / or fatty alcohol ethoxylates, such.
  • B. a fatty alcohol mixture with a Ci 2 alkyl radical and Ci 4 alkyl radical (Ci 2 / Ci 4 fatty alcohol).
  • Component b) may furthermore preferably contain a potassium and / or sodium alkylarylsulfonate having one or more, preferably one or two sulfonate groups, one or more, preferably one or two, alkyl groups having 5 to 18 C atoms, preferably 12 to 18 C atoms, and one or more, preferably one or two benzene rings.
  • Component c) comprises corrosion inhibitors, as are common for deicers and / or anti-icing agents based on glycols and water.
  • Suitable corrosion inhibitors are alkali metal phosphates, lower alkyl phosphates such as ethyl phosphate, dimethyl phosphate, isopropyl phosphate and the like, imidazoles such as 1H-imidazole, methylimidazole, benzimidazole and the like, and triazoles such as benzotriazole and tolyltriazole.
  • Thiourea, sodium nitrate or butyne-1,4-diol can also be used.
  • Dendritic polymers are highly branched globular polymers known in the art, and these polymers synthesized from multifunctional monomers fall into two distinct categories, the “dendrimers” and the “hyperbranched polymers.” Dendrimers have a very regular radially symmetric structure In contrast to the dendrimers, they are polydispersed and irregular in their branching and structure In addition to the dendritic and terminal units, in hyperbranched polymers, in addition to dendrimers, linear units also occur.
  • Dendritic Polymers "John Wiley & Sons, Ltd., West Wales, UK 2001 as well b) Jikei M., Kakimoto M. "Hyperbranched Polymers: A Promising New Class of Materials” Prog. Polym. Sei., 26 (2001) 1233-1285 and / or
  • the dendritic polymers described in these publications are also preferred for the purposes of the present invention. Furthermore, it is preferred that the dendritic polymers belong to the class of hyperbranched polymers and preferably at least 3 repeat units per molecule, preferably at least 10 repeat units per molecule, further preferably at least 100 repeat units per molecule, more preferably at least 200 repeat units and furthermore preferably at least 400 repeat units each having at least three, preferably at least four bonding options, wherein at least 3 of these repeat units, more preferably at least 10 and more preferably at least 20 are each connected via at least three, preferably at least four binding possibilities with at least three, preferably at least four further repeat units , Sometimes the dendritic polymers have a maximum of 10,000, preferably a maximum of 5,000 and more preferably a maximum of 2,500 repeat units.
  • the dendritic polymer has at least three repeat units which each have at least three possible bonding possibilities, wherein at least three of these repeat units have at least two possible bonding possibilities.
  • the term "repeating unit” is to be understood as meaning an always recurring structure within the dendritic molecule
  • the term "possibility of bonding” is preferably understood as meaning the functional structure within a repeating unit with which a link to another repeating unit is possible.
  • the repeating unit is a structure with at least three binding possibilities (X, Y, Z):
  • the linking of the monomer units with one another can be achieved by polycondensation, by polyaddition, by free-radical polymerization, by anionic polymerization, by cationic polymerization
  • Group transfer carried out by coordinative polymerization or by ring-opening polymerization.
  • the dendritic polymer has a solubility in a glycol-water mixture (particularly preferably 50 parts by weight glycol / 50 parts by weight water) of at least 0.1 g, preferably at least 1.0 g and more preferably at least 2.0 g, each based on 100 , 0 g glycol-water mixture.
  • the solubility is preferably determined at 25 ° C.
  • the measurement of this solubility can be carried out according to the so-called piston method, wherein the solubility of the pure substance in the solvent is measured.
  • the substance solids must be pulverized
  • the solution is cooled and held at the test temperature. The solution is stirred until the equilibrium is reached.
  • the measurement can be performed immediately at the test temperature, if it is ensured by appropriate sampling that the saturation equilibrium is reached. Then the concentration of the test substance in the solution, which must not contain any undissolved substance particles, is determined by a suitable analytical method.
  • the dendritic polymer contains polyether, polyetheramide, polyetherimide,
  • Polyethersulfone polyester, polyesteramide, polyesterimide, polyamide, polyamidoamine,
  • Polyurea-urethane polyglycerol, polyvinylidene fluoride, polysulfoneamine, polyethylenimine, polyacrylic,
  • Polyacrylate, polysiloxane, polyethersiloxane, polyimide and / or Polymethacrylathowen wherein for the purposes of the present invention polyester, Polyesteramid- and / or Polyethererritten have proven particularly useful.
  • the proportion of these units is expediently 2 to 10,000, preferably 2 to 5,000 and particularly preferably 2 to 3,000.
  • the dendritic polymer has NH 2 end groups. In a second particularly preferred embodiment, the dendritic polymer has COOH end groups.
  • the dendritic polymer has OH end groups.
  • the dendritic polymer preferably has a weight average molecular weight Mw in the range from 300 g / mol to 100,000 g / mol, favorably in the range from 300 g / mol to 50,000 g / mol, particularly preferably in the range from 300 g / mol to 40,000 g / mol, in particular in the range of 300 g / mol to 20,000 g / mol.
  • the determination of the molecular weight in particular the determination of the weight average molecular weight Mw and the number average molecular weight Mn, can in known manner, for. B. by means
  • GPC Gel permeation chromatography
  • the number average molecular weight can also be determined by steam or membrane osmosis, the z. In K.F. Arndt; G. Müller; Polymer characterization; Hanser Verlag 1996 (steam pressure osmosis) and H. -G. Elias, macromolecules structure synthesis properties, Wegig & Wepf Verlag 1990 (membrane osmosis) are described in more detail.
  • the polydispersity Mw / Mn of preferred dendritic polymers is in the range of 1-50, favorably in the range of 1-40, more preferably in the range of 1-20, in particular in the range of 1-10.
  • the degree of branching of the dendritic polymer is expediently in the range of> 0.0% to 85.0%, preferably in the range of> 0.0% to 75.0%, in particular in the range of> 0.0% to 65.0%. , According to a particularly preferred embodiment, the degree of branching of the dendritic polymer is greater than 10.0%, preferably greater than 20.0%, in particular greater than 25.0%.
  • the degree of branching can be determined according to Frey or Frechet. A detailed description of these methods is given in D. Hoelter, A. Burgath, H. Frey, Acta Polymer, 1997, 48, 30, and H. Magnusson, E. Malmström, A. Huit, M. Joansson, Polymer 2002, 43, 301.
  • inventively employable dendritic polymers are already commercially available under the brand Boltorn ® from Perstorp AB hyperbranched polyester, polyether or polyester are / ether, the hyperbranched available as Polymin® ®, Lupasol ® and / or PEI ® from BASF AG Polyethyleneimines and the hyperbranched polyester amides available under the brand Hybrane ® from DSM BV, Netherlands particularly favorable.
  • dendritic polymer examples include hyperbranched polyglycerols of the company Hyperpolymers with 800 g / mol ⁇ Mw ⁇ 40,000 g / mol eg with the type designation PG-2, PG-5 and PG-6 and polyethyleneimines with the type designation PEI-5 and PEI-25 from Hyperpolymers GmbH.
  • Another example of a particularly suitable hyperbranched polymer are Epomin® brand polyimines from Nippon Shokubai Co., Ltd.
  • Component e) is another preferably water-soluble thickener.
  • Component f) is preferably a basic pH regulator from the group of alkali metal hydroxides, such as NaOH and KOH, the alkylamines, such as butylamine, hexylamine, octylamine and isononylamine, and the alkanolamines, such as mono-, di- and triethanolamine.
  • alkali metal hydroxides are particularly preferred.
  • the component g) is preferably an acidic pH regulator from the group of inorganic or organic acids, such as phosphoric acid, phosphorous acid, mono- and dicarboxylic acids having alkyl groups having 2 to 12 carbon atoms, preferably 4 to 8 carbon atoms, and a or more, preferably one or two benzene rings.
  • a deicing and / or anti-icing agent such an acidic pH regulator, its content is preferably from 0.1 wt .-% to 5.0 wt .-%, based on the Weight of the deicing agent and / or anti-icing agent.
  • the deicing composition and / or anti-icing agent according to the invention preferably contains at least 5.0% by weight, more preferably at least 10.0% by weight, of water.
  • the deicing agent and / or anti-icing agent may contain defoamers, dyes, complexing agents and antioxidants.
  • Anti-icing agent has a comparatively high quiescent viscosity. This is preferably in the range from 3,000 mPas to 60,000 mPas, preferably in the range from 3,500 mPas to 50,000 mPas and particularly preferably in the range from 4,000 mPas to 40,000 mPas. It is preferably measured at 0.3 rpm and 20 0 C.
  • the deicing composition and / or anti-icing agent according to the invention exhibits a comparatively low flow viscosity. This is preferably less than 1500 mPas, preferably less than 1200 mPas and particularly preferably less than 1000 mPas. It is preferably measured at 60 rpm and 20 0 C.
  • the deicing composition according to the invention and / or anti-icing agent after mechanical stress has no appreciable irreversible viscosity loss.
  • the agent Comparing the quiescent viscosity of the agent before and after the mechanical stress, the agent usually loses no more than 30%, preferably not more than 25% and most preferably not more than 20% of its original viscosity.
  • Thickener molecule through the narrow gap between the rotor and stator pressed through, where they can be irreversibly damaged depending on the thickener type.
  • the resulting loss of viscosity leads to a reduction in the retention time.
  • the completely dried-out deicing composition and / or anti-icing agent should as far as possible not form any residues that swell by rehydration to poorly soluble gels.
  • B aluminum sheets of 2024-T3 material with a surface of 100 mm x 50 mm x 1 mm are used. The surface of the sheets is preferably aged by alternating brief immersion in each sodium hydroxide solution and nitric acid, so that fluid and Gelruckstande can adhere better.
  • the aluminum sheet is expediently immersed for four seconds completely in the fluid to be examined and then dried at a temperature between 30 0 C and 35 ° C. This step is repeated six times with the same sheet after 24 hours. Within this first test phase, a dry residue gradually forms on the aluminum surface.
  • the sheet is immersed with the dried fluid pressure, preferably for 30 seconds in demineralized water and carefully pulled back out of the water. After preferably 60 seconds, the weight of the sheet is weighed with the swollen fluid pressure. This rehydration step is conveniently repeated ten times in total.
  • the deicing and / or anti-icing agent of the present invention also has a superior property profile. Usually all will complies with further requirements of the SAE specification AMS 1428. Thus, the anti-icing time (WSET test) of these agents is usually greater than 30 minutes. The 1: 1 dilution with water usually shows a retention time of more than 5 minutes. The discharge behavior of all concentrations to be tested in the wind tunnel generally corresponds to the minimum requirement for all required temperatures. In addition, all other material testing tests are normally fulfilled.
  • the preparation of the anti-icing and anti-icing agent according to the invention can be carried out in a manner known per se by mixing the components.
  • two reference anti-icing and anti-icing agents are prepared by mixing the following components:
  • the anti-icing and anti-icing agent obtained was examined for viscosity (Haake Rheo Stress 600 / Cylinder System Z40 DIN).
  • the components were dissolved by vigorous stirring at room temperature over 3 h.
  • the obtained anti-icing and anti-icing agent was examined for viscosity.
  • Dendritic polyether obtained as described in WO 00/56802 (Mw: 3800 g / mol, OH number: 260-300 mg KOH / g, polydispersity M w / M n : 1.4, viscosity (23 0 C, 30 l / s): 25 Pas).
  • the components were dissolved by vigorous stirring at room temperature over 3 h.
  • the obtained anti-icing and anti-icing agent was examined for viscosity.
  • the components were dissolved by vigorous stirring at room temperature over 3 h.
  • the obtained anti-icing and anti-icing agent was examined for viscosity.

Abstract

L'invention concerne un agent de dégivrage ou antigivre contenant (par rapport au poids total) entre 35 et 95% en poids d'au moins un glycol, entre 0,001 et 5% en poids d'au moins un polymère dendritique, entre 0,01 et 5% en poids d'au moins un agent épaississant supplémentaire et éventuellement de l'eau. L'invention concerne également l'utilisation d'une quantité comprise entre 0,001 et 5% en poids d'au moins un polymère dendritique, d'une quantité comprise entre 0,01 et 5% en poids d'au moins un agent épaississant supplémentaire destiné à épaissir la composition contenant entre 35 et 95% en poids d'au moins un glycol et éventuellement de l'eau.
PCT/EP2007/056895 2006-08-26 2007-07-06 Agent de dégivrage et/ou antigivre WO2008025589A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2009526000A JP2010501692A (ja) 2006-08-26 2007-07-06 除氷剤及び／又は防氷剤
AT07787177T ATE466062T1 (de) 2006-08-26 2007-07-06 Enteisungsmittel und/oder vereisungsschutzmittel
EP07787177A EP2054483B1 (fr) 2006-08-26 2007-07-06 Agent de dégivrage et/ou antigivre
CA002661262A CA2661262A1 (fr) 2006-08-26 2007-07-06 Agent de degivrage et/ou antigivre
DE502007003618T DE502007003618D1 (fr) 2006-08-26 2007-07-06
US12/310,318 US7875203B2 (en) 2006-08-26 2007-07-06 Deicing agent and/or anti-icing agent

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006040122A DE102006040122B3 (de) 2006-08-26 2006-08-26 Enteisungsmittel und/oder Vereisungsschutzmittel
DE102006040122.0 2006-08-26

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Publication Number Publication Date
WO2008025589A1 true WO2008025589A1 (fr) 2008-03-06

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US (1) US7875203B2 (fr)
EP (1) EP2054483B1 (fr)
JP (1) JP2010501692A (fr)
CN (1) CN101506326A (fr)
AT (1) ATE466062T1 (fr)
CA (1) CA2661262A1 (fr)
DE (2) DE102006040122B3 (fr)
RU (1) RU2009110729A (fr)
WO (1) WO2008025589A1 (fr)

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CN113801633A (zh) * 2020-06-15 2021-12-17 中国石油化工股份有限公司 一种防冰液及其制备方法和应用
CN113789152B (zh) * 2021-10-12 2023-09-05 西安热工研究院有限公司 一种可喷洒于风电叶片表面的抑冰剂及其制备方法
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CA2661262A1 (fr) 2008-03-06
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DE102006040122B3 (de) 2007-10-31
RU2009110729A (ru) 2010-10-10
ATE466062T1 (de) 2010-05-15
EP2054483A1 (fr) 2009-05-06
DE502007003618D1 (fr) 2010-06-10
JP2010501692A (ja) 2010-01-21
EP2054483B1 (fr) 2010-04-28
US20090309061A1 (en) 2009-12-17

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